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Issue 4, 2016
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Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles

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Abstract

The synthesis of polysubstituted hexahydroindoles through trienamine-organocatalyzed cycloadditions of pyrrolidinyl dienals, prepared by palladium-catalyzed cycloisomerization, is reported. The cycloadditions of this novel class of dienals proceed with excellent levels of enantio- and diastereoselectivity, with the regioselectivity of cycloaddition with respect to the tethering ring readily tuned through design of the cycloisomerization substrate. This work culminates in the first examples of double-stereodifferentiating trienamine catalysis, where catalyst stereocontrol dominates facial selectivity in the cycloaddition, affording azacyclic products that are specifically functionalized at every position.

Graphical abstract: Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles

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Publication details

The article was received on 28 Oct 2015, accepted on 05 Nov 2015 and first published on 11 Nov 2015


Article type: Communication
DOI: 10.1039/C5CC08886K
Citation: Chem. Commun., 2016,52, 693-696
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    Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles

    V. Chintalapudi, E. A. Galvin, R. L. Greenaway and E. A. Anderson, Chem. Commun., 2016, 52, 693
    DOI: 10.1039/C5CC08886K

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